N. Morin et al., A simple model for RPLC retention and selectivity of imidazole enantiomersusing beta-cyclodextrin as chiral selector, CHROMATOGR, 48(5-6), 1998, pp. 388-394
Using reversed phase liquid chromatography (RPLC), this paper investigates
the enantioselectivity variations, in a series of weak polar R, S-imidazole
derivatives, with beta-cyclodextrin concentration in the mobile phase over
a wide range of column temperatures. These compounds are used for the trea
tment of onychomycosis. The selectivity data obtained were assessed using a
chiral recognition model, based on the formation of complexes between the
solute molecule and the cyclodextrin cavity. Gibbs Helmholtz parameters (De
lta(Delta H), Delta(Delta S)) between R- and S- enantiomers were determined
from the logarithm of the separation factor, alpha, versus the reciprocal
of the temperature plots. The thermodynamic results predicted that the enan
tioselectivity mechanism was related to both the solute's bulkiness and the
asymmetric carbon atom configuration.